WO2015012528A2 - Composé organique et élément électroluminescent organique le comprenant - Google Patents

Composé organique et élément électroluminescent organique le comprenant Download PDF

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WO2015012528A2
WO2015012528A2 PCT/KR2014/006456 KR2014006456W WO2015012528A2 WO 2015012528 A2 WO2015012528 A2 WO 2015012528A2 KR 2014006456 W KR2014006456 W KR 2014006456W WO 2015012528 A2 WO2015012528 A2 WO 2015012528A2
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aryl
formula
alkyl
boron
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WO2015012528A3 (fr
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김태형
이용환
박호철
이창준
신진용
백영미
엄민식
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주식회사 두산
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Definitions

  • the present invention relates to a novel organic compound and an organic electroluminescent device comprising the same.
  • the organic electroluminescent device when a voltage is applied between two electrodes, holes are injected into the organic material layer from the anode and electrons from the cathode. When the injected holes and electrons meet, excitons are formed, and when the excitons fall to the ground, they shine.
  • the material used as the organic material layer may be classified into a light emitting material, a hole injection material, a hole transport material, an electron transport material, an electron injection material and the like according to its function.
  • the light emitting materials may be classified into blue, green, and red light emitting materials, and yellow and orange light emitting materials for better natural colors according to light emission colors.
  • a host / dopant system may be used as the light emitting material.
  • the dopant material may be divided into a fluorescent dopant using an organic material and a phosphorescent dopant using a metal complex compound containing heavy atoms such as Ir and Pt. Since the development of the phosphor can theoretically improve the luminous efficiency up to four times as compared to the fluorescent material, attention has been focused on not only the phosphorescent dopant material but also the phosphorescent host material.
  • hole injection materials hole transport materials.
  • NPB, BCP, Alq 3 and the like are known as hole blocking materials and electron transporting materials
  • anthracene derivatives are known as fluorescent dopant / host materials among light emitting materials.
  • metal complex compounds including Ir such as Firpic, Ir (ppy) 3 , and (acac) Ir (btp) 2 are known.
  • CBP is known as a phosphorescent dopant material which has an advantage in terms of efficiency improvement among light emitting materials.
  • the conventional light emitting materials are good in terms of the light emission characteristics, but because the glass transition temperature is low, the thermal stability is not very good, it is not a satisfactory level in terms of the life of the organic EL device. Therefore, there is a demand for development of a light emitting material having excellent performance.
  • An object of the present invention is to provide a novel organic compound excellent in light emitting ability, hole transporting ability and hole injection ability.
  • the present invention is the novel organic It is another object of the present invention to provide an organic electroluminescent device including a compound having a low driving voltage, high luminous efficiency, and an improved lifetime.
  • the present invention provides a compound represented by the following formula (1).
  • R 1 and R 2 , R 2 and R 3 , or R 3 and R 4 forms a condensed ring represented by the following Formula 2,
  • R 1 to R 5 which do not form a condensed ring is Each independently hydrogen, deuterium, halogen, cyano group, nitro group, C 1 -C 40 alkyl group, C 3 -C 40 cycloalkyl group, nuclear atom 3-40 heterocycloalkyl group, C 6 -C 60 aryl group, nuclear atoms aryl of from 5 to 60 heteroaryl group, C 1 ⁇ C 40 alkyloxy group of, C 6 ⁇ C 60 aryloxy group, C group 3 ⁇ C 40 alkylsilyl, C 6 ⁇ aryl of C 60 silyl group, C 2 ⁇ C 40 group of an alkyl boron, C 6 ⁇ C group 60 arylboronic of, C 6 ⁇ C 60 aryl phosphine group, C 6 ⁇ aryl phosphine
  • a dotted line means a site where condensation occurs with the compound of Chemical Formula 1
  • R 6 to R 9 are each independently hydrogen, deuterium, halogen, cyano group, nitro group, C 1 ⁇ C 40 alkyl group, C 3 ⁇ C 40 cycloalkyl group, nuclear hetero atoms 3 to 40 heterocycloalkyl group, C 6 ⁇ C 60 aryl group, nuclear atoms 5 to 60 heteroaryl group, C 1 ⁇ C 40 alkyloxy group, C 6 ⁇ C 60 aryloxy group, C 3 ⁇ C 40 alkylsilyl group, C 6 ⁇ C 60 arylsilyl group, C 2 ⁇ C 40 alkyl boron group, C 6 ⁇ C 60 aryl boron group, C 6 ⁇ C 60 aryl phosphine group, C 6 ⁇ C 60 aryl phosphine oxide group and C 6 ⁇ C 60 It is selected from the group consisting of an arylamine group, wherein at least one of
  • L 1 is a single bond, an arylene group having 6 to 60 carbon atoms or a heteroarylene group having 5 to 60 nuclear atoms,
  • X 1 is selected from the group consisting of O, S, Se and NAr 3 ,
  • Y 1 and Y 2 are each independently N or CR 10 ,
  • R 10 and R 21 to R 24 are each independently hydrogen, deuterium, halogen, cyano group, nitro group, C 1 -C 40 alkyl group, C 3 -C 40 cycloalkyl group, and nuclear atom 3 to 40 heterocyclo Alkyl group, C 6 ⁇ C 60 Aryl group, Nuclear 5 to 60 heteroaryl group, C 1 ⁇ C 40 Alkyloxy group, C 6 ⁇ C 60 Aryloxy group, C 3 ⁇ C 40 Alkylsilyl Group, C 6 ⁇ C 60 arylsilyl group, C 2 ⁇ C 40 alkyl boron group, C 6 ⁇ C 60 aryl boron group, C 6 ⁇ C 60 aryl phosphine group, C 6 ⁇ C 60 aryl force It may be selected from the group consisting of a pin oxide group and an arylamine group of C 6 ⁇ C 60 , or may be combined with adjacent groups to form a condensed ring,
  • Ar 1 to Ar 3 are each independently an aryl group having 6 to 18 carbon atoms or a heteroaryl group having 5 to 18 nuclear atoms,
  • Heteroaryl group, alkyloxy group, aryloxy group, alkylsilyl group, arylsilyl group, alkyl boron group, aryl boron group, aryl phosphine group, aryl phosphine oxide group and arylamine group are each independently deuterium, halogen, cyan Furnace group, C 1 to C 40 alkyl group, C 3 to C 40 cycloalkyl group, nuclear atom 3 to 40 heterocycloalkyl group, C 6 to C 60 aryl group, nuclear atom 5 to 60 heteroaryl group, C 1 ⁇ C 40 alkyloxy group, C 6 ⁇ C 60 aryloxy group, C 1 ⁇ C 40 alkylsilyl group, C 6 ⁇ C 60 arylsilyl group, C 2 ⁇ C 40 alkyl boron group, aryl of C 6 ⁇ C 60 boron group, C 6 ⁇ C 60 aryl phosphine group, C 6
  • the present invention is an organic electroluminescent device comprising an anode, a cathode and at least one organic layer interposed between the anode and the cathode, at least one of the at least one organic layer is a compound represented by the formula (1) It provides an organic electroluminescent device characterized in that it comprises.
  • At least one organic material layer including the compound represented by Chemical Formula 1 is selected from the group consisting of a hole transporting layer, a hole injection layer and a light emitting layer, preferably a hole transporting layer and / or a light emitting layer, more preferably a light emitting layer.
  • the compound represented by Chemical Formula 1 may be a phosphorescent host of the emission layer.
  • 'alkyl' used in the present invention means a monovalent functional group obtained by removing a hydrogen atom from a straight or branched chain saturated hydrocarbon having 1 to 40 carbon atoms.
  • Non-limiting examples thereof include methyl, ethyl, propyl, isobutyl, sec-butyl, pentyl, iso-amyl, hexyl and the like.
  • 'Alkenyl' used in the present invention means a monovalent functional group obtained by removing a hydrogen atom from a straight or branched chain unsaturated hydrocarbon having 2 to 40 carbon atoms having at least one carbon-carbon double bond.
  • Non-limiting examples thereof include vinyl, allyl, isopropenyl, 2-butenyl and the like.
  • 'Alkynyl' used in the present invention means a monovalent functional group obtained by removing a hydrogen atom from a straight or branched chain unsaturated hydrocarbon having 2 to 40 carbon atoms having at least one carbon-carbon triple bond.
  • Non-limiting examples thereof include ethynyl, 2-propynyl and the like.
  • 'cycloalkyl' means a monovalent functional group obtained by removing a hydrogen atom from a monocyclic or polycyclic non-aromatic hydrocarbon having 3 to 40 carbon atoms (saturated cyclic hydrocarbon).
  • Non-limiting examples thereof include cyclopropyl, cyclopentyl, cyclohexyl, norbornyl, adamantine and the like.
  • Heterocycloalkyl' as used herein means a monovalent functional group obtained by removing a hydrogen atom from a non-aromatic hydrocarbon (saturated cyclic hydrocarbon) having 3 to 40 atoms, and preferably at least one carbon in the ring, preferably 1 to 3 carbons are substituted with a hetero atom such as N, O or S.
  • Non-limiting examples thereof include morpholine, piperazine and the like.
  • 'Aryl' used in the present invention means a monovalent functional group obtained by removing a hydrogen atom from a single ring or a C 6-60 aromatic hydrocarbon in which two or more rings are combined.
  • the two or more rings may be attached in a simple or condensed form with each other.
  • Non-limiting examples thereof include phenyl, biphenyl, terphenyl, naphthyl, phenanthryl, anthryl and the like.
  • Heteroaryl' used in the present invention is a monovalent functional group obtained by removing a hydrogen atom from a monoheterocyclic or polyheterocyclic aromatic hydrocarbon having 5 to 60 nuclear atoms, and at least one carbon in the ring, preferably 1 To 3 carbons are substituted with heteroatoms such as nitrogen (N), oxygen (O), sulfur (S) or selenium (Se).
  • the heteroaryl may be attached in a form in which two or more rings are simply attached or condensed with each other, and may also include a condensed form with an aryl group.
  • heteroaryls include six-membered monocyclic rings such as pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl; Polycyclics such as phenoxathienyl, indolinzinyl, indolyl, purinyl, quinolyl, benzothiazole, carbazolyl ring; And 2-furanyl, N-imidazolyl, 2-isoxazolyl, 2-pyridinyl, 2-pyrimidinyl, and the like.
  • 'Alkoxyoxy' used in the present invention means a monovalent functional group represented by RO-, wherein R is alkyl having 1 to 40 carbon atoms, and has a linear, branched or cyclic structure. It may include. Non-limiting examples of such alkyloxy include methoxy, ethoxy, n-propoxy, 1-propoxy, t-butoxy, n-butoxy, pentoxy and the like.
  • 'Aryloxy' used in the present invention means a monovalent functional group represented by R'O-, wherein R 'is an aryl having 6 to 60 carbon atoms.
  • R ' is an aryl having 6 to 60 carbon atoms.
  • Non-limiting examples of such aryloxy include phenyloxy, naphthyloxy, diphenyloxy and the like.
  • 'alkylsilyl' means silyl substituted with alkyl having 1 to 40 carbon atoms
  • 'arylsilyl' means silyl substituted with aryl having 6 to 60 carbon atoms
  • arylamine has 6 to 60 carbon atoms. Amine substituted with aryl.
  • the term 'condensed ring' refers to a condensed aliphatic ring, a condensed aromatic ring, a condensed heteroaliphatic ring, a condensed heteroaromatic ring, or a combination thereof.
  • the novel organic compound according to the present invention is an indole-based moiety at the end of a pyrazolocarbazole moiety condensed with an indazole-based moiety and an indole-based moiety.
  • an indole-based moiety condensed pyrazolocarbazole-based moiety is directly bonded or by a linking group (e.g. arylene group, etc.) to form a basic skeleton,
  • a linking group e.g. arylene group, etc.
  • the compound represented by the formula (1) has a higher molecular weight than the material (for example, 4,4-dicarbazolybiphenyl (hereinafter referred to as 'CBP')) applied to the conventional organic electroluminescent device has a high glass transition temperature, thermal stability great.
  • the material for example, 4,4-dicarbazolybiphenyl (hereinafter referred to as 'CBP')
  • 'CBP' 4,4-dicarbazolybiphenyl
  • the host material included in the phosphorescent layer should have a triplet energy gap of the host higher than that of the dopant material.
  • the lowest excited state of the host material must be higher in energy than the lowest emission state of the dopant material.
  • energy levels may be effectively controlled by introducing various substituents into condensed pyrazolocarbazole moieties having a wide singlet energy level and a high triplet energy level.
  • the compound represented by the formula (1) is effective in suppressing the crystallization of the organic material layer.
  • the compound represented by Chemical Formula 1 has a structure in which an electron withdrawal group (EWG) having high electron absorbing property is coupled, and thus the binding force between holes and electrons can be enhanced because the whole molecule has a bipolar characteristic.
  • EWG electron withdrawal group
  • the compound represented by Chemical Formula 1 may improve the phosphorescence property of the organic EL device and improve hole injection / transport ability, emission efficiency, driving voltage, lifetime characteristics, and the like. Accordingly, the electron transport ability and the like can also be improved. Accordingly, the compound represented by Chemical Formula 1 according to the present invention is an organic material layer material of the organic electroluminescent device, preferably a light emitting layer material (blue, green and / or red phosphorescent host material), a hole transport layer material and a hole injection layer material Can be used.
  • the compound represented by the formula (1) of the present invention is preferably selected from the group consisting of the compound represented by the formula (1a) to 1f.
  • Ar 1 , Ar 2 and R 1 to R 9 in Chemical Formulas 1a to 1f are as defined in Chemical Formula 1. At least one of R 6 to R 9 is represented by Chemical Formula 3, and R 8 is particularly preferably represented by Chemical Formula 3.
  • L 1 is preferably linked to R 23 in R 21 to R 24 .
  • Formula 3 is preferably selected from the group consisting of structures represented by the following Formulas 3a to 3h.
  • X 1 , Y 1 , Y 2 and R 21 to R 24 in Chemical Formulas 3a to 3h are the same as defined in Chemical Formula 3.
  • X 1 is preferably NAr 3
  • X 2 is selected from the group consisting of O, S, Se and NAr 4 , and among them, NAr 4 is preferred.
  • Y 3 and Y 4 are each independently N or CR 12 , wherein Y 3 and Y 4 are both If CR 12, a plurality of CR 12 may be the same or different from each other.
  • R 12 and R 25 are each independently hydrogen, deuterium, halogen, cyano group, C 1 ⁇ C 40 alkyl group, C 6 ⁇ C 40 aryl group, nuclear atom 5 to 40 heteroaryl group, C 6 ⁇ C 40 aryloxy group C 1 to C 40 alkyloxy group, C 6 to C 40 arylamine group, C 1 to C 40 alkylsilyl group, C 1 to C 40 alkylboron group, C 6 to C group 40 arylboronic of, C 6 ⁇ C 40 aryl phosphine group, C 6 ⁇ C 40 aryl phosphine oxide group, and a C 6 ⁇ C 40 selected from an aryl silyl group the group consisting of or the adjacent groups bonded to the condensed ring of Can be formed.
  • Ar 4 is an aryl group having 6 to 18 carbon atoms or a heteroaryl group having 5 to 18 nuclear atoms, and m is an integer of 0 to 4.
  • the aryl group and heteroaryl group of Ar 4 the alkyl group, aryl group, heteroaryl group, aryloxy group, alkyloxy group, arylamine group, alkylsilyl group, alkyl boron group and aryl boron of R 12 and R 25 .
  • the group, the arylphosphine group, the arylphosphine oxide group and the arylsilyl group are each independently deuterium, halogen, cyano group, C 1 ⁇ C 40 alkyl group, C 3 ⁇ C 40 cycloalkyl group, nuclear atom 3 to 40 hetero Cycloalkyl group, C 6 ⁇ C 60 aryl group, C 5 ⁇ C 60 heteroaryl group, C 1 ⁇ C 40 Alkyloxy group, C 6 ⁇ C 60 Aryloxy group, C 1 ⁇ C 40 Alkyl Silyl group, C 6 ⁇ C 60 arylsilyl group, C 2 ⁇ C 40 alkyl boron group, C 6 ⁇ C 60 aryl boron group, C 6 ⁇ C 60 aryl phosphine group, C 6 ⁇ C 60 aryl It may be substituted with one or more substituents selected from the group consisting of a phosphine oxide group and a C 6 ⁇ C 60 arylamine
  • substituents selected from the group consisting of deuterium, halogen, cyano group, C 1 ⁇ C 40 alkyl group, C 6 ⁇ C 60 aryl group and heteroaryl group of 5 to 60 nuclear atoms.
  • substituents selected from the group consisting of deuterium, halogen, cyano group, C 1 ⁇ C 40 alkyl group, C 6 ⁇ C 60 aryl group and heteroaryl group of 5 to 60 nuclear atoms.
  • a plurality of substituents may be the same or different from each other.
  • Ar 1 to Ar 3 are each independently an aryl group having 6 to 18 carbon atoms or a heteroaryl group having 5 to 18 nuclear atoms, wherein at least one is represented by the following Formula 4 desirable.
  • * means a site bonded to Chemical Formulas 1,2 and 3
  • L 2 is a single bond
  • Z is 1 to Z 5 are each independently N or CR 11 , wherein at least one of Z 1 to Z 5 is N
  • R 11 is hydrogen, deuterium, halogen, cyano group, C 1 ⁇ C 40 alkyl group, C 6 ⁇ C 40 aryl group, C 3 ⁇ C 40 cycloalkyl group, a 3 to 40 nuclear atoms of a heterocycloalkyl group, Nuclear atoms of 5 to 40 heteroaryl group, C 6 ⁇ C 40 of the aryloxy C 1 ⁇ C 40 alkyloxy group of, C 6 ⁇ C 40 aryl amine group, C 1 ⁇ C 40 alkyl silyl group, C 1 ⁇ C 40 group of an alkyl boron, C 6 ⁇ C 40 aryl boron group
  • Aryl boron group, aryl silyl group, aryl phosphine group and aryl phosphine oxide group are each independently deuterium, halogen, cyano group, C 1 ⁇ C 40 alkyl group, C 3 ⁇ C 40 cycloalkyl group, nuclear atom 3 to 40 heterocycloalkyl groups, C 6 to C 60 aryl groups, 5 to 60 heteroaryl groups, C 1 to C 40 alkyloxy groups, C 6 to C 60 aryloxy groups, C 1 to C 40 alkylsilyl group, C 6 ⁇ C 60 arylsilyl group, C 2 ⁇ C 40 alkyl boron group, C 6 ⁇ C 60 aryl boron group, C 6 ⁇ C 60 aryl phosphine group, C 6 ⁇ C aryl phosphine oxide group, and a C 6 ⁇ least one member selected from the group consisting of an aryl amine of the C 60 substituent of 60 can be replaced.
  • the formula 4 is more preferably selected from the group consisting of the structures represented by A-1 to A-15.
  • L 2 and R 11 are the same as defined in Formula 4, wherein a plurality of R 11 is the same as or different from each other,
  • R 26 is hydrogen, deuterium, halogen, cyano group, C 1 ⁇ C 40 alkyl group, C 6 ⁇ C 40 aryl group, nuclear 5 to 40 heteroaryl group, C 6 ⁇ C 40 aryloxy group C 1 ⁇ C 40 alkyloxy group of, C 6 ⁇ C 40 aryl amine group, C 1 ⁇ C 40 groups of the alkyl silyl group, C 1 ⁇ C 40 alkyl, boron, C 6 ⁇ C 40 group of the arylboronic, C 6 ⁇ C 40 aryl phosphine group, C 6 ⁇ C 40 aryl phosphine oxide group, and a C 6 ⁇ C 40 aryl selected from the group consisting of a silyl or, by combining groups of adjacent, may form a condensed ring,
  • n is an integer of 0-4.
  • the groups are each independently deuterium, halogen, cyano group, C 1 ⁇ C 40 alkyl group, C 2 ⁇ C 40 alkenyl group, C 2 ⁇ C 40 alkynyl group, C 6 ⁇ C 40 aryl group, nuclear atom 5 To 40 heteroaryl group, C 6 to C 40 aryloxy group, C 1 to C 40 alkyloxy group, C 6 to C 40 arylamine group, C 3 to C 40 cycloalkyl group, nuclear atom number 3 to 40 heterocycloalkyl group, C 1 ⁇ C 40 alkyl silyl of the group, C 1 ⁇ C 40 group of an alkyl boro
  • Ar 1 to Ar 3 that is not represented by the general formula (4) is a C 6 ⁇ C 18 aryl group or a heteroaryl group of 5 to 18 nuclear atoms, and among these, a phenyl group, acridine group, or 1,3 It is more preferable that it is a, 5-triazine group.
  • L 1 and L 2 are each independently a single bond, or preferably a phenylene group or a biphenylene group.
  • the compound represented by Chemical Formula 1 of the present invention may be specifically represented by the following compounds (C1 to C60), but is not limited thereto.
  • the present invention provides an organic electroluminescent device comprising a compound represented by the formula (1).
  • the present invention is an organic electroluminescent device comprising an anode, a cathode, and at least one organic layer interposed between the anode and the cathode, wherein at least one of the at least one organic layer It includes a compound represented by the formula (1).
  • the compound represented by Formula 1 may be used alone or in combination of two or more.
  • the at least one organic material layer may be any one or more of a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer and an electron injection layer, wherein the organic material layer containing the compound represented by the formula (1) is preferably a light emitting layer.
  • the emission layer of the organic electroluminescent device according to the present invention may include a host material, and may include a compound represented by Chemical Formula 1 as the host material.
  • a compound represented by Chemical Formula 1 is included as a light emitting layer material of the organic electroluminescent device, preferably a green phosphorescent host, the binding force between the holes and the electrons in the light emitting layer increases, so the efficiency (luminescence efficiency and power efficiency) of the organic electroluminescent device is increased. ), Lifespan, brightness and driving voltage can be improved.
  • the structure of the organic EL device according to the present invention is not particularly limited, and may be, for example, a structure in which a substrate, an anode, a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, and a cathode are sequentially stacked.
  • at least one of the hole injection layer, the hole transport layer, the light emitting layer, the electron transport layer and the electron injection layer may include a compound represented by the formula (1), preferably the light emitting layer may include a compound represented by the formula (1). have.
  • the compound of the present invention may be used as a phosphorescent host material of the emission layer.
  • the electron injection layer may be further stacked on the electron transport layer.
  • the structure of the organic electroluminescent device of the present invention may be a structure in which an anode, one or more organic material layers and a cathode are sequentially stacked, and an insulating layer or an adhesive layer is inserted at an interface between the electrode and the organic material layer.
  • the organic electroluminescent device of the present invention may be formed using other materials and methods known in the art, except that at least one of the organic material layers (eg, the light emitting layer) is formed to include the compound represented by Chemical Formula 1. It may be prepared by forming an organic material layer and an electrode.
  • the organic material layer may be formed by a vacuum deposition method or a solution coating method.
  • the solution coating method include, but are not limited to, spin coating, dip coating, doctor blading, inkjet printing, or thermal transfer.
  • the substrate may be a silicon wafer, quartz, a glass plate, a metal plate, a plastic film and a sheet, but is not limited thereto.
  • the anode material may be a metal such as vanadium, chromium, copper, zinc, gold or an alloy thereof; Metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), indium zinc oxide (IZO); Combinations of metals and oxides such as ZnO: Al or SnO 2 : Sb; Conductive polymers such as polythiophene, poly (3-methylthiophene), poly [3,4- (ethylene-1,2-dioxy) thiophene] (PEDT), polypyrrole or polyaniline; And carbon black, but are not limited thereto.
  • Metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), indium zinc oxide (IZO); Combinations of metals and oxides such as ZnO: Al or SnO 2 : Sb
  • Conductive polymers such as polythiophene, poly (3-methylthiophene), poly [3,4- (ethylene-1,2-dioxy) thiophene] (PEDT),
  • the negative electrode material may be a metal such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, or lead or an alloy thereof; And multilayer structure materials such as LiF / Al or LiO 2 / Al, and the like.
  • IC-1 (6.97 g, 13.29 mmol), bromobenzene (4.17 g, 26.57 mmol), Cu powder (0.17 g, 2.66 mmol), K 2 CO 3 (3.66 g, 26.57 mmol) obtained in Preparation Example 1 under a nitrogen stream, Na 2 SO 4 (3.78 g, 26.57 mmol) and nitrobenzene (100 ml) were mixed and stirred at 190 ° C. for 12 h.
  • a target compound C was prepared by the same procedure as in Synthesis Example 1, except that 4- (3-bromophenyl) dibenzo [b, d] thiophene (9.01 g, 26.57 mmol) was used instead of bromobenzene in Synthesis Example 1. -3 (7.80 g, yield 75%) was obtained.
  • IC-2 (6.97 g, 13.29 mmol) obtained in Preparation Example 2 was used instead of IC-1 used in Synthesis Example 1, and 2-bromo-4-phenylquinazoline (7.58 g, 26.57 mmol) was used instead of bromobenzene. Then, the same procedure as in Synthesis Example 1 was performed to obtain C-7 (7.94 g, yield 82%) as a target compound.
  • a glass substrate coated with ITO (Indium tin oxide) having a thickness of 1500 mm 3 was ultrasonically cleaned with distilled water. After washing the distilled water, ultrasonic cleaning with a solvent such as isopropyl alcohol, acetone, methanol, dried, transferred to a UV OZONE cleaner (Power sonic 405, Hwashin Tech), and then the substrate using UV for 5 minutes The substrate was cleaned and transferred to a vacuum evaporator.
  • a solvent such as isopropyl alcohol, acetone, methanol
  • a green organic electroluminescent device was manufactured in the same manner as in Example 1, except that CBP was used instead of Compound C-1 used as a host material of the emission layer in Example 1.
  • the structure of CBP used is as follows.
  • Example 1 Host material Drive voltage (V) Emission Peak (nm) Current efficiency (cd / A)
  • Example 1 Compound C-1 6.50 517 42.0
  • Example 2 Compound C-2 6.55 519 42.1
  • Example 3 Compound c-3 6.50 519 42.0
  • Example 4 Compound c-4 6.50 517 42.3
  • Example 5 Compound C-5 6.55 516 41.8
  • Example 6 Compound c-6 6.60 518 42.1
  • Example 7 Compound c-7 6.50 518 42.0
  • Example 8 Compound c-8 6.55 519 41.5
  • Example 9 Compound c-9 6.55 517 42.0
  • Example 10 Compound C-10 6.60 517 41.8
  • Example 11 Compound C-11 6.59 517 41.7
  • Example 12 Compound c-12 6.45 518 42.1
  • Example 13 Compound C-13 6.50 520 42.0
  • Example 14 Compound c-14 6.60 519 41.6
  • Example 15 Compound c-15 6.60 519 41.6
  • Example 16 Compound c
  • the green organic electroluminescent devices (Examples 1 to 18, respectively) using the compounds represented by Formula 1 according to the present invention (Compounds C-1 to C-18) as phosphorescent host materials of the emission layer
  • the obtained green organic electroluminescent element was found to have superior current efficiency and drive voltage as compared to the green organic electroluminescent element (the organic electroluminescent element of Comparative Example 1) using CBP as a material of the light emitting layer.
  • the compound according to the present invention can be used as an organic material layer material of the organic electroluminescent device, preferably a hole injection layer material, a hole transport layer material or a light emitting layer material because of excellent heat resistance, hole injection ability, hole transporting ability, light emitting ability and the like.
  • the organic electroluminescent device including the compound according to the present invention in the hole injection layer, the hole transport layer, and / or the light emitting layer may greatly improve aspects of light emission performance, driving voltage, lifetime, efficiency, and the like, and thus, full color display. It can be effectively applied to panels.

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  • Electroluminescent Light Sources (AREA)

Abstract

La présente invention concerne un nouveau composé et un élément électroluminescent organique le comprenant. Le composé selon la présente invention peut améliorer le rendement lumineux, la tension d'attaque, la durée de vie et similaire d'un élément électroluminescent du fait qu'il est utilisé dans une couche de matériau organique, de préférence une couche d'émission de lumière, de l'élément électroluminescent organique.
PCT/KR2014/006456 2013-07-22 2014-07-16 Composé organique et élément électroluminescent organique le comprenant WO2015012528A2 (fr)

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KR102358032B1 (ko) * 2017-05-23 2022-02-03 솔루스첨단소재 주식회사 유기 화합물 및 이를 포함하는 유기 전계 발광 소자

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